Journal
ORGANIC LETTERS
Volume 22, Issue 15, Pages 5885-5889Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01982
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Funding
- Science and Technology Innovation Commission of Shenzhen Municipality [JCYJ20180302180256215]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002, Y01216129]
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Despite extensive investigations, altering the regioselectivity of atom transfer radical addition (ATRA) to alkynes remains a highly desirable yet unachieved challenge. Guided by computational predictions, thiosulfonates were found herein as a tunable radical precursor for thiyl radicals instead of well-recognized sulfonyl radicals. Merging such a finding with ATRA to phenylacetylenes leads to a highly regio- and stereoselective approach to (E)-beta-arylsulfonylvinyl sulfides. This protocol is feathered by mild conditions, low photocatalyst loading, no transition-metal catalyst required, and broad functional group compatibility. The successful application of our protocol in the late-stage functionalization of bioactive natural product derivatives demonstrates its synthetic utility. Mechanistic studies corroborate the photoredox-catalyzed ATRA pathway and reveal the pivotal role of thiyl radical, to which unprecedented regioselectivity was attributed.
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